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Synthesis of the chromophores of fluorescent proteins and their analogs

Abstract

Members of the green fluorescent protein (GFP) family are widely used in experimental biology as genetically encoded fluorescent tags. Chromophores of GFP-like proteins share a common structural core: 3,5-dihydro-4H-imidazol-4-one. This review covers synthetic approaches to 3,5-dihydro-4H-imida-zol-4-ones, substituted at different positions. General, as well as specific methods, represented by single examples are considered. The most popular synthetic route to substituted 3,5-dihydro-4H-imidazol-4-ones includes synthesis of azlactones, followed by transformation into N-acyldehydroamino acids and, finally, cyclization into target heterocycles. Accordingly, the review is divided into three parts: the first part covers syntheses of azlactones, the second part covers main approaches to N-acyldehydroamino acids, and in the third part we summarize cyclizations of N-acyldehydroamino acids, as well as all other approaches to 3,5-dihydro-4H-imidazol-4-ones.

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Abbreviations

Ar:

aryl

CDI:

carbonyldiimidazole

DABCO:

1,4-diazabicyclo[2,2,2]octane

DBU:

diazabicycloundecene

DDQ:

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DEAD:

diethyl azodicarboxylate

imidazolone:

5-arylene-3,5-dihydro-4H-imi-dazole-4-one

DIPEA:

diisopropylethylamine

GFP:

green flu-orescent protein

HOBt:

1-hydroxybenzotriazole

LDA:

lithium diisopropylamide

MS:

molecular sieves

oxazolone:

5-arylidene-3,5-dihydro-4H-oxazol-4-one

NBS:

N-bromosuccineimide

PMB:

p-methoxybenzyl

Py:

pyridine

TBDMS:

tert-butyldime-thylsilyl

Ts:

tosyl

FP:

fluorescent protein

References

  1. Chudakov, D.M., Matz, M.V., Lukyanov, S., and Lukyanov, K.A., Physiol. Rev., 2010, vol. 90, pp. 1103–1163.

    PubMed  CAS  Article  Google Scholar 

  2. Ivashkin, P.E., Yampolsky, I.V., and Lukyanov, K.A., Russ. J. Bioorg. Chem., 2009, vol. 35, pp. 652–669.

    CAS  Article  Google Scholar 

  3. Subach, F.V. and Verkhusha, V.V., Chem. Rev., 2012, vol. 112, pp. 4308–4327.

    PubMed  CAS  Article  Google Scholar 

  4. Heim, R., Prasher, D.C., and Tsien, R.Y., Proc. Natl. Acad. Sci. U.S.A., 1994, vol. 91, pp. 12501–12504.

    PubMed  CAS  Article  Google Scholar 

  5. Tomosugi, W., Matsuda, T., Tani, T., Nemoto, T., Kotera, I., Saito, K., Horikawa, K., and Nagai, T., Nat. Methods, 2009, vol. 6, pp. 351–353.

    PubMed  CAS  Article  Google Scholar 

  6. Cody, C.W., Prasher, D.C., Westler, W.M., Prendergast, F.G., and Ward, W.W., Biochemistry, 1993, vol. 32, pp. 1212–1218.

    PubMed  CAS  Article  Google Scholar 

  7. Chattoraj, M., King, B.A., Bublitz, G.U., and Boxer, S.G., Proc. Natl. Acad. Sci. U.S.A., 1996, vol. 93, pp. 8362–8367.

    PubMed  CAS  Article  Google Scholar 

  8. Kogure, T., Karasawa, S., Araki, T., Saito, K., Kinjo, M., and Miyawaki, A., Nat. Biotechnol., 2006, vol. 24, pp. 577–581.

    PubMed  CAS  Article  Google Scholar 

  9. Henderson, J.N., Osborn, M.F., Koon, N., Gepshtein, R., Huppert, D., and Remington, S.J., J. Am. Chem. Soc., 2009, vol. 131, pp. 13212–13213.

    PubMed  CAS  Article  Google Scholar 

  10. Piatkevich, K.D., Malashkevich, V.N., Almo, S.C., and Verkhusha, V.V., J. Am. Chem. Soc., 2010, vol. 132, pp. 10762–10770.

    PubMed  CAS  Article  Google Scholar 

  11. Ward, W.W. and Bokman, S., H., Biochemistry, 1982, vol. 21, pp. 4535–4540.

    PubMed  CAS  Article  Google Scholar 

  12. Palm, G.J., Zdanov, A., Gaitanaris, G.A., Stauber, R., Pavlakis, G.N., and Wlodawer, A., Nat. Struct. Biol., 1997, vol. 4, pp. 361–365.

    PubMed  CAS  Article  Google Scholar 

  13. Brejc, K., Sixma, T.K., Kitts, P.A., Kain, S.R., Tsien, R.Y., Ormo, M., and Remington, S.J., Proc. Natl. Acad. Sci. U.S.A., 1997, vol. 94, pp. 2306–2311.

    PubMed  CAS  Article  Google Scholar 

  14. Agmon, N., Biophys. J., 2005, vol. 88, pp. 2452–2461.

    PubMed  CAS  Article  Google Scholar 

  15. Niwa, H., Inouye, S., Hirano, T., Matsuno, T., Kojima, S., Kubota, M., Ohashi, M., and Tsuji, F., Proc. Natl. Acad. Sci. U.S.A., 1996, vol. 93, pp. 13617–13 622.

    PubMed  CAS  Article  Google Scholar 

  16. Yampolsky, I.V., Remington, S.J., Martynov, V.I., Potapov, V.K., Lukyanov, S.A., and Lukyanov, K.A., Biochemistry, 2005, vol. 44, pp. 5788–5793.

    PubMed  CAS  Article  Google Scholar 

  17. Yampolsky, I.V., Kislukhin, A.A., Amatov, T.T., Shcherbo, D., Potapov, V.K., Lukyanov, S., and Lukyanov, K.A., Bioorg. Chem., 2008, vol. 36, pp. 96–104.

    PubMed  CAS  Article  Google Scholar 

  18. Yampolsky, I.V., Balashova, T.A., and Lukyanov, K.A., Biochemistry, 2009, vol. 48, pp. 8077–8082.

    PubMed  CAS  Article  Google Scholar 

  19. Ivashkin, P.E., Lukyanov, K.A., Lukyanov, S.A., and Yampolsky, I.V., J. Org. Chem., 2011, vol. 76, pp. 2782–2791.

    PubMed  CAS  Article  Google Scholar 

  20. Palmer, C.D., The Chemistry of Heterocyclic Compounds, Vol. 60: Oxazoles: Synthesis, Reactions, and Spectroscopy, Part B, Weinheim: Wiley-VCH Verlag GmbH, KGaA, 2004.

    Google Scholar 

  21. Erlenmeyer, E.J., Justus Lieb. Ann. der Chem., 1893, vol. 275, pp. 1–8.

    Article  Google Scholar 

  22. Perkin, W.H., J. Chem. Soc., 1868, vol. 21, pp. 181–186.

    Article  Google Scholar 

  23. Cativiela, C., Diaz-De-Villegas M.D., Melendez E., J. Het. Chem., 1985, vol. 22, pp. 1655–1657.

    CAS  Article  Google Scholar 

  24. Ryuichi, K., Tsunetoshi, H., Kunio, H., Masayoshi, O., Mariko, H., Masafumi, F., and Toshio, F., J. Med. Chem., 1995, vol. 14, pp. 2728–2742.

    Google Scholar 

  25. Cornforth, J. and Hui, D., J. Chem. Soc. PT1, 1990, vol. 5, pp. 1459–1462.

    Google Scholar 

  26. Winton, D.J., J. Chem. Soc. PT1, 1981, pp. 344–346.

    Google Scholar 

  27. Marrian, D.H., Russell, P.B., and Todd, A.R., Biochem. J., 1949, vol. 45, pp. 533–537.

    PubMed  CAS  Google Scholar 

  28. Kidwai, M. and Kumar, R., Org. Prep. Proced. Int., 1998, vol. 4, pp. 451–453.

    Article  Google Scholar 

  29. Gelmi, M.L., Clerici, F., and Melis, A., Tetrahedron, 1997, vol. 53, pp. 1843–1854.

    CAS  Article  Google Scholar 

  30. Kokai, T.K., Chem. Abstr., 1982, vol. 96, p. 142836.

    Google Scholar 

  31. Rao, P.S. and Venkataratnam, R.V., Indian J. Chem. Sect., vol. 33, pp. 984–985.

  32. Zavyalov, S.I., Dorofeyeva, O.V., and Rumyantseva, Y.Y., Chem. Abstr., 1995, vol. 122, p. 31378.

    Google Scholar 

  33. Topuzyan, V.O. and Khachvankyan, G.Y., Chem. Abstr., 1998, vol. 128, p. 321583.

    Google Scholar 

  34. Wang, Y., Shi, D., Lu, Z., and Dai, G., Synth. Commun., 2000, vol. 30, pp. 707–712.

    CAS  Article  Google Scholar 

  35. Gaset, A. and Gorrichon, J.P., Synth. Commun., 1982, vol. 12, pp. 71–79.

    CAS  Article  Google Scholar 

  36. Boruah, A., Baruah, P.P., and Sandhu, J.S., J. Chem. Res. Synop., 1998, pp. 614–615.

    Google Scholar 

  37. Slater, G. and Somerville, A.W., Tetrahedron, 1966, vol. 22, pp. 35–42.

    CAS  Article  Google Scholar 

  38. Haasbroeka, P.P., Oliverb, D.W., and Carpyc, A.J., J. Mol. Struct., 2004, vol. 690, pp. 89–94.

    Article  CAS  Google Scholar 

  39. Arrieta, A., Cossio, F.P., and Palomo, C., Tetrahedron, 1985, vol. 41, pp. 1703–1712.

    CAS  Article  Google Scholar 

  40. Khosropour, A.R., Khodaei, M.J., and Hoseini, J., J. Het. Chem., 2008, vol. 3, pp. 683–686.

    Article  Google Scholar 

  41. Cabaret, D., Liu, J., and Wakselman, M., Synthesis, 1994, vol. 5, pp. 480–483.

    Article  Google Scholar 

  42. Melhado, A.D., Luparia, M., and Dean, F.T., J. Am. Chem. Soc., 2007, vol. 129, pp. 12638–12639.

    PubMed  CAS  Article  Google Scholar 

  43. Hoyng, C.F., Mckenna, M.G., and Walters, D.L., Synthesis, 1982, vol. 3, pp. 191–193.

    Article  Google Scholar 

  44. Hashimoto, M., Matsumoto, M., and Terashima, S., Tetrahedron, 2003, vol. 59, pp. 3041–3062.

    CAS  Article  Google Scholar 

  45. Ritter, T., Kvæno, L., Werder, M., Hauser, H., and Carreira, E.M., Org. Biomol. Chem., 2005, vol. 3, pp. 3514–3523.

    PubMed  CAS  Article  Google Scholar 

  46. Takacs, E., Berente, Z., Hada, V., Maho, S., Kollar, L., and Skoda-Foldes, R., Tetrahedron, 2009, vol. 65 P, pp. 4659–4663.

    Article  CAS  Google Scholar 

  47. Kumar, P., Mishra, H.D., and Mukerjee, A.K., Synthesis, 1980, vol. 10, pp. 836–839.

    Article  Google Scholar 

  48. Tripathy, P.K. and Mukerjee, A.K., Synthesis, 1985, vol. 3, pp. 285–288.

    Article  Google Scholar 

  49. Charles, S.C. and Burt, C.P., J. Am. Chem. Soc., 1955, vol. 77, pp. 1544–1546.

    Article  Google Scholar 

  50. El-Hashash, M.A., Afify, A.A., Kaddah, A.M., and El-Kady, S.S., Synthesis, 1981, vol. 10, p. 798.

    Article  Google Scholar 

  51. Crawford, M. and Little, W.T., J. Chem. Soc., 1959, pp. 729–732.

    Google Scholar 

  52. Mestdagh, H. and Pancrazi, A., Tetrahedron, 1984, vol. 40, pp. 3399–3413.

    CAS  Article  Google Scholar 

  53. Terence, C.C., Charles, R.F., Omima, N., and Andrew, W., J. Am. Chem. Soc., 1980, vol. 102, pp. 6828–6837.

    Article  Google Scholar 

  54. Kuroda, Y., Ueda, H., Nozawa, H., and Ogoshi, H., Tetrahedron Lett., 1997, vol. 38, pp. 7901–7904.

    CAS  Article  Google Scholar 

  55. Arief, M.M., Phosphorus, Sulfur and Silicon, 1997, vol. 127, pp. 159–165.

    CAS  Article  Google Scholar 

  56. Aly, A.A., J. Het. Chem., 2008, vol. 45, pp. 993–998.

    CAS  Article  Google Scholar 

  57. Cornforth, J. and Hui, D., J. Chem. Soc. PT1, 1991, pp. 2183–2187.

    Google Scholar 

  58. Attenburrow, J., Elliott, D.F., and Penny, G.F., J. Chem. Soc., 1948, pp. 310–318.

    Google Scholar 

  59. Nestor, J.J., Ho, T.L., Simpson, R.A., Horner, B.L., Jones, G.H., McRae, G.I., and Vickery, B.H., J. Med. Chem., 1982, vol. 7, pp. 795–801.

    Article  Google Scholar 

  60. Chandrasekhar, S. and Karri, P., Tetrahedron Lett., 2007, vol. 48, pp. 785–786.

    CAS  Article  Google Scholar 

  61. Dhar, S.L. and Singh, A., Tetrahedron Lett., 2003, vol. 44, pp. 5637–5640.

    Article  CAS  Google Scholar 

  62. Conway, P.A., Devine, K., and Paradisi, F., Tetrahedron, 2009, vol. 65, pp. 2935–2938.

    CAS  Article  Google Scholar 

  63. Dhar, S.L., Rai, V.K., and Yadav, B.S., Tetrahedron, 2009, vol. 65, pp. 1306–1315.

    Article  CAS  Google Scholar 

  64. Graham, D.W., Ashton, W.T., Barash, L., Brown, J.E., Brown, R.D., Canning, L.F., Chen, A., Springer, J.P., and Rogers, E.F., J. Med. Chem., 1987, vol. 304, pp. 1074–1090.

    Article  Google Scholar 

  65. O’Brien, J.L. and Niemann, C., J. Am. Chem. Soc., 1957, vol. 79, pp. 80–85.

    Article  Google Scholar 

  66. Mauldin, S.C., Hornback, W.J., and Munroe, J.E., J. Chem. Soc. PT1, 2001, vol. 13, pp. 1554–1558.

    Google Scholar 

  67. Ward, D.E., Vazquez, A., and Soledade, M.C., J. Org. Chem., 1999, vol. 64, pp. 1657–1666.

    PubMed  CAS  Article  Google Scholar 

  68. Carter, H.E., Handler, P., and Melville, D.B., J. Biol. Chem., 1939, vol. 129, pp. 359–371.

    CAS  Google Scholar 

  69. Toshishige, I., Bull. Chem. Soc. Jpn., 1972, vol. 45, p. 1254.

    Article  Google Scholar 

  70. Pines, S.H., Kozlowski, M.A., and Karady, S., J. Org. Chem., 1969, vol. 34, pp. 1621–1627.

    CAS  Article  Google Scholar 

  71. Carter, H.E. and Risser, W.C., J. Biol. Chem., 1941, vol. 139, pp. 255–262.

    CAS  Google Scholar 

  72. Torino, D., Mollica, A., Pinnen, F., Feliciani, F., Lucente, G., Fabrizi, G., Portalone, G., Davis, P., Lai, J., Ma, S.-W., Porreca, F., and Hruby, V.J., J. Med. Chem., 2010, vol. 11, pp. 4550–4555.

    Article  CAS  Google Scholar 

  73. Breitholle, E.G. and Stammer, C.H., J. Org. Chem., 1976, vol. 41, pp. 1344–1349.

    PubMed  CAS  Article  Google Scholar 

  74. Lott, R.S., Breitholle, E.G., and Stammer, C.H., J. Org. Chem., 1980, vol. 6, pp. 1151–1153.

    Article  Google Scholar 

  75. McCapra, F., Razavi, Z., and Neary, A.P., J. Chem. Soc. Chem. Commun., 1988, vol. 12, pp. 790–791.

    Article  Google Scholar 

  76. Riordan, J.M. and Stammer, C.H., Tetrahedron Lett., 1971, vol. 12, pp. 4969–4972.

    Article  Google Scholar 

  77. Doherty, D.G., Tietzman, J.E., and Bergmann, M., J. Biol. Chem., 1943, vol. 147, pp. 617–637.

    CAS  Google Scholar 

  78. Phelps, D.J. and Gaeta, F.C., Synthesis, 1982, vol. 3, pp. 234–235.

    Article  Google Scholar 

  79. Shaw, K.N., Mcmillan, A., Gudmudson, A.G., and Armstrong, M.D., J. Org. Chem., 1958, vol. 23, pp. 1171–1178.

    CAS  Article  Google Scholar 

  80. Sheehan, J.C. and Duggins, W.E., J. Am. Chem. Soc., 1950, vol. 72, pp. 2475–2477.

    CAS  Article  Google Scholar 

  81. Molina, P., Fresneda, P.M., and Hurtado, F., Synth. Commun., 1987, vol. 17, pp. 485–490.

    CAS  Article  Google Scholar 

  82. Molina, P., Tarraga, A., and Lidon, M.J., J. Chem. Soc. PT1, 1990, pp. 1727–1731.

    Google Scholar 

  83. Mustafa, A., Asker, W., Hamid, A., Khalifa, E., and Zayed, E.M., Justus Lieb. Ann. der Chem., 1968, vol. 713, pp. 151–161.

    CAS  Article  Google Scholar 

  84. Schmidt, C.L.A., The Chemistry of the Amino Acids and Proteins, Springfield, Ill., 1944.

    Google Scholar 

  85. Plöchl, J., Chem. Ber., 1884, pp. 1616–1624.

    Google Scholar 

  86. Alkaabi, S.S. and Shawal, A.S., Can. J. Chem., 1992, vol. 10, pp. 2515–2519.

    Article  Google Scholar 

  87. Phelps, D.J., Godreau, P.V., and Nicholas, E.S., J. Chem. Soc. PT2, 1981, pp. 140–142.

    Google Scholar 

  88. Shaw, E. and Mcdowell, J., J. Am. Chem. Soc., 1949, vol. 71, pp. 1691–1698.

    CAS  Article  Google Scholar 

  89. Khan, N.H., Synth. Commun., 1978, vol. 8, pp. 497–510.

    Article  Google Scholar 

  90. Cativiela, C., Garcia, J.I., and Melendez, E., Synthesis, 1982, vol. 9, pp. 763–765.

    Article  Google Scholar 

  91. Pelger, R. and Markert, G., Chem. Ber., 1957, vol. 90, pp. 1494–1499.

    Article  Google Scholar 

  92. Kartar, S.N. and Jnanendra, N.R., J. Chem. Soc., 1931, pp. 976–980.

    Google Scholar 

  93. Stafforst, T. and Diederichsen, U., Eur. J. Org. Chem., 2007, vol. 6 P, pp. 899–911.

    Article  CAS  Google Scholar 

  94. Tu, S., Zhang, J., Jia, R., Zhang, Y., Jiang, B., and Shi, F., Synthesis, 2007, vol. 4, pp. 558–565.

    Article  CAS  Google Scholar 

  95. Guo, Y.-M., Oike, H., Saeki, N., and Aida, N., Ang. Chem., 2004, vol. 116, pp. 5023–5026.

    Article  Google Scholar 

  96. Rahman, A.N., Khalil, A.M., and Manna, M.A., Phosphorus, Sulfur and Silicon, 1991, vol. 60, nos. 3‐4, p. 159.

    Article  Google Scholar 

  97. Hughes, A.B., Amino Acids, Peptides and Proteins in Organic Chemistry, vol. 1: Origins and Synthesis of Amino Acids, Weinheim: Wiley-VCH Verlag GmbH, KGaA, 2009.

    Google Scholar 

  98. Bonauer, C., Walenzyk, T., and Konig, B., Synthesis, 2006, vol. 1, pp. 1–21.

    Google Scholar 

  99. Schmidt, U., Lieberknecht, A., and Wild, J., Synthesis, 1988, vol. 3, pp. 159–173.

    Article  Google Scholar 

  100. Manis, P.A. and Rathke, M.W., J. Org. Chem., 1980, vol. 24 P, pp. 4952–4954.

    Article  Google Scholar 

  101. Moriya, N., Yoneda, N., Miyoshi, M., and Matsumoto, K., J. Org. Chem., 1982, vol. 1, pp. 94–98.

    Article  Google Scholar 

  102. Zupet, R. and Tisler, M., J. Org. Chem., 1994, vol. 2, pp. 507–508.

    Article  Google Scholar 

  103. Goodall, K. and Parsons, A.F., Tetrahedron Lett., 1995, vol. 36, pp. 3259–3260.

    CAS  Article  Google Scholar 

  104. Li, K.W., Wu, J., Xing, W., and Simon, J.A., J. Am. Chem. Soc., 1996, vol. 118, pp. 7237–7238.

    CAS  Article  Google Scholar 

  105. Cherney, R.J. and Wang, L., J. Org. Chem., 1996, vol. 61, pp. 2544–2546.

    CAS  Article  Google Scholar 

  106. Somekh, L. and Shanzer, A., J. Org. Chem., 1983, vol. 48, pp. 907–908.

    CAS  Article  Google Scholar 

  107. Sai, H., Ogiku, T., and Ohmizu, H., Synthesis, 2003, vol. 2, pp. 201–205.

    Article  Google Scholar 

  108. Miller, M., J. Org. Chem., 1980, vol. 45, pp. 3131–3132.

    CAS  Article  Google Scholar 

  109. Wulff, G. and Bohnke, H., Ang. Chem., 1984, vol. 96, pp. 362–363.

    CAS  Google Scholar 

  110. Ferreira, P.M.T., Maia, H.L.S., Monteiro, L.S., and Sacramento, J., J. Chem. Soc. PT1, 1999, pp. 3697–3703.

    Google Scholar 

  111. Stohlmeyer, M.M., Tanaka, H., and Wandless, N.J., J. Am. Chem. Soc., 1999, vol. 121, pp. 6100–6102.

    CAS  Article  Google Scholar 

  112. Rich, D.H. and Tam, J.P., J. Org. Chem., 1977, vol. 42, pp. 3815–3820.

    PubMed  CAS  Article  Google Scholar 

  113. Walter, R. and Roy, I., J. Org. Chem., 1971, vol. 36, pp. 2561–2563.

    PubMed  CAS  Article  Google Scholar 

  114. Horikawa, E., Kodaka, M., Nakahara, Y., Okuno, H., and Nakamura, K., Tetrahedron Lett., 2001, vol. 42, pp. 8337–8339.

    CAS  Article  Google Scholar 

  115. Grim, M.D., Chauhan, V., Shimohigashi, Y., Kolar, A.J., and Stammer, C.H., J. Org. Chem., 1981, vol. 46, pp. 2671–2673.

    CAS  Article  Google Scholar 

  116. Manis, P.A. and Rathke, M.W., J. Org. Chem., 1980, vol. 45, pp. 4952–4954.

    CAS  Article  Google Scholar 

  117. Graham, D.W., Ashton, W.T., Barash, L., Brown, J.E., Brown, R.D., Canning, L.F., Chen, A., Springer, J.P., and Rogers, E.F., J. Med. Chem., 1987, vol. 6, pp. 1074–1090.

    Article  Google Scholar 

  118. Labia, R. and Morin, C., J. Org. Chem., 1986, vol. 51, pp. 249–251.

    CAS  Article  Google Scholar 

  119. Adamczyk, M., Akireddy, S.R., and Reddy, R.E., Org. Lett., 2001, vol. 3, pp. 3157–3159.

    PubMed  CAS  Article  Google Scholar 

  120. Krause, N., Hoffmann-Roder, A., and Canisius, J., Synthesis, 2002, vol. 12, pp. 1759–1775.

    Article  Google Scholar 

  121. Choi, J., Shin, J.E., and Chun, K.H., Bull. Korean Chem. Soc., 1999, vol. 20, pp. 1123–1126.

    CAS  Google Scholar 

  122. Kimura, R., Nagano, T., and Kinoshita, H., Bull. Chem. Soc. Jpn., 2002, vol. 75, pp. 2517–2525.

    CAS  Article  Google Scholar 

  123. Buck, R.T., Clarke, P.A., Coe, D.M., Drysdale, M.J., Ferris, L., Haigh, D., Moody, C.J., Pearson, N.D., and Swann, E., Chem.-Eur. J., 2000, vol. 6, pp. 2160–2167.

    PubMed  CAS  Article  Google Scholar 

  124. Xu, F., Zacuto, M., Yoshikawa, N., Desmond, R., Hoerrner, S., Itoh, T., Journet, M., Humphrey, G.R., Cowden, C., Strotman, N., and Devine, P., J. Org. Chem., 2010, vol. 75, pp. 7829–7841.

    CAS  Article  Google Scholar 

  125. Enders, D., Chen, Z., and Raabe, G., Synthesis, 2005, vol. 2, pp. 306–311.

    Article  CAS  Google Scholar 

  126. Oesterle, T. and Simchen, G., Synthesis, 1985, vol. 4, pp. 403–406.

    Article  Google Scholar 

  127. Seethaler, T. and Simchen, G., Synthesis, 1986, vol. 5, pp. 390–392.

    Article  Google Scholar 

  128. Nagano, T. and Kinoshita, H., Bull. Chem. Soc. Jpn., 2000, vol. 73, pp. 1605–1613.

    CAS  Article  Google Scholar 

  129. Burk, M.J., Allen, J.G., Kiesman, W., and Stoffan, K.M., Tetrahedron Lett., 1997, vol. 38, pp. 1309–1312.

    CAS  Article  Google Scholar 

  130. Kitagawa, F., Murase, M., and Kitamura, N., J. Org. Chem., 2002, vol. 15, pp. 2524–2531.

    Article  CAS  Google Scholar 

  131. Abreu, A.S., Ferreira, P.M., Queiroz, M.J., and Gatto, E., Sonogashira, Eur. J. Org. Chem., 2004, vol. 10, pp. 3985–3991.

    Article  CAS  Google Scholar 

  132. Granacher, C. and Gulbas, G., Helv. Chim. Acta, 1927, vol. 10, pp. 819–826.

    CAS  Article  Google Scholar 

  133. Petersen, A., Riber, P., Andersen, L.H., and Brondsted, N., Synthesis, 2007, vol. 23, pp. 3635–3638.

    Google Scholar 

  134. Chen, K.Y., Cheng, Y.-M., Cheng-Hsuan, L., Che Ng-Chih, H., Mei-Lin, H., Lee, G., and Chou, P.T., J. Am. Chem. Soc., 2007, vol. 129, pp. 4534–4535.

    PubMed  CAS  Article  Google Scholar 

  135. Pruger, P. and Bach, Y., Synthesis, 2007, vol. 7, pp. 1103–1106.

    Google Scholar 

  136. Xiang, H., Alasdair, F.B., and Tonge, P.J., Org. Lett., 2002, vol. 9, pp. 1523–1526.

    Google Scholar 

  137. Erlenmeyer, E., Chem. Ber., 1900, vol. 33, pp. 2036–2041.

    CAS  Article  Google Scholar 

  138. Lykkeberg, J. and Klitgaard, N.A., Acta Chem. Scand., 1972, vol. 26, pp. 2687–2694.

    CAS  Article  Google Scholar 

  139. McCapra, F., Razavi, Z., and Neary, A.P., J. Chem. Soc., 1988, vol. 12, pp. 790–791.

    Google Scholar 

  140. Yang, J.-S., Huang, G.-J., Liu, I.-H., and Peng, S.-M., Chem. Commun., 2008, vol. 11, pp. 1344–1346.

    Article  CAS  Google Scholar 

  141. Bhatt, P.V., Wadla, W., Rain, I.M., and Pravin, M.P., Het. Comm., 2006, vol. 1, pp. 79–82.

    Google Scholar 

  142. Lee, C., Chen, Y., Lin, H., Jhong, Y., Chang, C., Tsai, C., Kao, C., and Chien, N., Tetrahedron, 2012, vol. 68, pp. 5898–5907.

    CAS  Article  Google Scholar 

  143. Mazaahir, K. and Mohan, R., J. Chin. Chem. Soc., 2003, vol. 50, pp. 1075–1078.

    Google Scholar 

  144. Cativiela, C. and Melendez, E., Hetereocycles, 1984, vol. 2, pp. 2775–2781.

    Google Scholar 

  145. Pradeer, K.T., A Facile, Synthesis, 1985, vol. 3 P, pp. 285–288.

    Google Scholar 

  146. Bondock, S., Khalifa, W., and Fadda, A.A., Synth. Commun., 2006, vol. 36, pp. 1601–1612.

    CAS  Article  Google Scholar 

  147. Zarif, M., El-Sheriff, H.A., and Tadros, M.E., Bull. Chem. Soc. Jpn., 1982, vol. 7, pp. 2267–2270.

    Google Scholar 

  148. Topuzyan, V.O., Arutyunyan, L.G., and Oganesyan, A.A., Russ. J. Org. Chem., 2007, vol. 6, pp. 868–871.

    Article  CAS  Google Scholar 

  149. Shimomura, O., FEBS Lett., 1979, vol. 104, pp. 220–222.

    CAS  Article  Google Scholar 

  150. Kidwai, A.R. and Devasia, G.M., J. Org. Chem., 1962, vol. 27, pp. 4527–4531.

    CAS  Article  Google Scholar 

  151. Lehr, H., Karlan, S., and Goldberg, M.W., J. Am. Chem. Soc., 1953, vol. 75, pp. 3640–3645.

    CAS  Article  Google Scholar 

  152. Kjaer, A., Acta Chem. Scand., 1953, vol. 7, pp. 1030–1035.

    CAS  Article  Google Scholar 

  153. Griffiths, G.J., Hauck, M.B., Imwinkelried, R., Kohr, J., Roten, C.A., and Stucky, G.C., J. Org. Chem., 1999, vol. 22, pp. 8084–8089.

    Article  CAS  Google Scholar 

  154. Janosik, T., Johnson, A.-L., and Dergman, G., Tetrahedron, 2002, vol. 58, pp. 2813–2819.

    CAS  Article  Google Scholar 

  155. Devasia, M., Tetrahedron Lett., 1976, vol. 17, pp. 571–572.

    Article  Google Scholar 

  156. Ekeley, J.B. and Ronzio, A.R., J. Am. Chem. Soc., 1935, vol. 57, pp. 1353–1356.

    CAS  Article  Google Scholar 

  157. Ito, Y., Inulushi, Y., and Saegusa, J., Synth. Commun., 1974, vol. 4, pp. 289–295.

    CAS  Article  Google Scholar 

  158. Brunken, J. and Bach, G., Chem. Ber., 1956, vol. 89, pp. 1363–1373.

    CAS  Article  Google Scholar 

  159. Ramachandra, S.H., Tetrahedron Lett., 1984, vol. 25, pp. 363–366.

    Article  Google Scholar 

  160. Goldschmidt, S. and Steigerwald, Ch., Chem. Ber., 1925, vol. 58, pp. 1346–1353.

    Google Scholar 

  161. Takeuchi, H., Hagiwara, S., and Eguchi, S., Tetrahedron, 1989, vol. 45, pp. 6375–6386.

    CAS  Article  Google Scholar 

  162. Barbosa, Y., Hart, D.J., and Magomedov, N.A., Tetrahedron, 2006, vol. 62, pp. 8748–8754.

    Article  CAS  Google Scholar 

  163. Wu, L. and Burgess, K., J. Am. Chem. Soc., 2008, vol. 130, pp. 4089–4096.

    PubMed  CAS  Article  Google Scholar 

  164. Baldridge, A., Solntsev, K.M., Song, C., Tanioka, N., Kowalik, J., Hardcastle, K., and Tolbert, L.M., Chem. Commun., 2010, vol. 46, pp. 5686–5688.

    CAS  Article  Google Scholar 

  165. Ruhemann, S. and Cunnington, A.V., J. Chem. Soc., 1899, vol. 75, pp. 954–963.

    CAS  Article  Google Scholar 

  166. Lerestif, J.M., Bazureau, J.P., and Hamelin, J., Tetrahedron Lett., 1993, vol. 49, pp. 4639–4642.

    Article  Google Scholar 

  167. Lerestif, J.M., Bazureau, J.P., and Hamelin, J., Tetrahedron, 1995, vol. 51, pp. 6757–6774.

    CAS  Article  Google Scholar 

  168. Yokoyama, M., Menjo, Y., and Togo, H., Synthesis, 1994, vol. 12, pp. 1467–1471.

    Article  Google Scholar 

  169. Kerneur, G., Lerestif, J.M., Bazureau, P., and Hamelin, J., Synthesis, 1997, vol. 3, pp. 287–290.

    Article  Google Scholar 

  170. Baldridge, A., Kowalik, J., and Tolbert, L.M., Synthesis, 2010, vol. 14, pp. 2424–2437.

    Google Scholar 

  171. Gong, X., Yang, H., Liu, H., Jiang, Y., Zhao, Y., and Fu, H., Org. Lett., 2010, vol. 14, pp. 3128–3131.

    Article  CAS  Google Scholar 

  172. Fresneda, P.M., Molina, P., and Sanz, M.A., Synlett, 2000, vol. 8, pp. 1190–1193.

    Google Scholar 

  173. Oumouch, S., Bourotte, M., Schmitt, M., and Bourguignon, J.-J., Synthesis, 2005, vol. 1, pp. 25–28.

    Google Scholar 

  174. Paige, J.S., Wu, K.Y., and Jaffrey, S.R., Science, 2011, vol. 333, pp. 642–646.

    PubMed  CAS  Article  Google Scholar 

  175. Paige, J.S., Nguyen-Duc, T., Song, W., and Jaffrey, S.R., Science, 2012, vol. 335, pp. 1194–1196.

    PubMed  CAS  Article  Google Scholar 

  176. Baldridge, A., Feng, S.H., Chang, Y.T., and Tolbert, L.M., Combinat. Chem., 2011, vol. 13, pp. 214–217.

    CAS  Google Scholar 

  177. Chuang, W.T., Chen, B.S., Chen, K.Y., Hsieh, C.C., and Chou, P.T., Chem. Commun., 2009, vol. 7, pp. 6982–6984.

    Article  CAS  Google Scholar 

  178. Baranov, M.S., Lukyanov, K.A., Borissova, A.O., Shamir, J., Kosenkov, D., Slipchenko, L.V., Tolbert, L.M., Yampolsky, I.V., and Solntsev, K.M., J. Am. Chem. Soc., 2012, vol. 134, pp. 6025–6032.

    PubMed  CAS  Article  Google Scholar 

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Correspondence to I. V. Yampolsky.

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Original Russian Text © M.S. Baranov, K.A. Lukyanov, I.V. Yampolsky, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 3, pp. 255–276.

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Baranov, M.S., Lukyanov, K.A. & Yampolsky, I.V. Synthesis of the chromophores of fluorescent proteins and their analogs. Russ J Bioorg Chem 39, 223–244 (2013). https://doi.org/10.1134/S1068162013030047

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Keywords

  • fluorescent protein
  • chromophore
  • GFP
  • azlactone
  • imidazolone